This conference paper explores the potential of Transition Design in addressing “wicked problems”, catalyzing societal transitions towards sustainable and resilient futures. By recognizing the interconnectedness of social, economic, and natural systems, the framework presents designers with a flexible strategy to integrate evolving design practices for systems-level change. It examines the efficacy of this approach through its application in a community-based intervention for sustainable food systems. The research presented builds upon existing transdisciplinary knowledge, practices and tools used to design societal transitions such as: visualizing the intricacies of a complex system; observing stakeholder relationships/ behaviors/ beliefs inherent in community contexts; co-creating alongside actors; identifying value chain pain points to situate immediate and long-term goals; enabling the practical implementation of interventions; ensuring place-based effectiveness, while considering global scalability. The employed methodology traces the wicked problem through multiple lenses, assessing a product, people, materiality, lifespan, finances, and supply chain dynamics.